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Comparative studies demonstrated that the effectiveness of elements <jats:bold>A<\/jats:bold>\u2013<jats:bold>D<\/jats:bold> in stabilization of the mesophase typically increases in the order: <jats:bold>B<\/jats:bold>&lt;<jats:bold>A<\/jats:bold>&lt;<jats:bold>C<\/jats:bold>&lt;<jats:bold>D<\/jats:bold>. Absorption and emission spectroscopy for the four series and reference compounds augmented with DFT computational results revealed that the degree of electronic interactions with the connected benzene \u03c0 system increases in the order <jats:bold>C<\/jats:bold>&lt;<jats:bold>A<\/jats:bold>&lt;<jats:bold>B<\/jats:bold>&lt;<jats:bold>D<\/jats:bold>. Emission spectra exhibit large Stokes\u2019 shifts for 10\u2010vertex derivatives (<jats:bold>B<\/jats:bold>) in solutions and in the solid state. Spectroscopic characterization was supplemented with polarization electronic spectroscopy and solvatochromic studies of selected series. Overall, 12\u2010vertex <jats:italic>p<\/jats:italic>\u2010carborane <jats:bold>A<\/jats:bold> acts as an electron withdrawing auxochromic substituent with interactions similar to those of bicyclo[2.2.2]octane, although capable of accepting some electron density in the excited state. In contrast, 10\u2010vertex <jats:italic>p<\/jats:italic>\u2010carborane <jats:bold>B<\/jats:bold> is much more interactive with the \u03c0\u2010aromatic electron manifold and exhibits greater ability to participate in photo\u2010induced CT processes. Absorption and emission energies and quantum yields (1\u201051\u2009%) for carborane derivatives, representing the D\u2212A\u2212D system, were compared to those of their isoelectronic zwitterionic analogues (the A\u2212D\u2212A system). 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